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WO 2018/197315 Al 01 November 2018 (01.11.2018) W !P O PCT

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WO 2018/197315 Al 01 November 2018 (01.11.2018) W !P O PCT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/197315 Al 01 November 2018 (01.11.2018) W !P O PCT (51) International Patent Classification: SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, C07D 471/04 (2006.01) A01N 43/90 (2006.01) TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (21) International Application Number: (84) Designated States (unless otherwise indicated, for every PCT/EP20 18/059973 kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, (22) International Filing Date: UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 19 April 2018 (19.04.2018) TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (25) Filing Language: English EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (26) Publication Langi English TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (30) Priority Data: KM, ML, MR, NE, SN, TD, TG). 20171 1014675 25 April 2017 (25.04.2017) IN 20171 10155 14 02 May 2017 (02.05.2017) IN Declarations under Rule 4.17: — as to applicant's entitlement to apply for and be granted a (71) Applicant: SYNGENTA PARTICIPATIONS AG patent (Rule 4.1 7(H)) [CH/CH]; Schwarzwaldallee 215, 4058 Basel (CH). — of inventorship (Rule 4.1 7(iv)) (72) Inventors: RENDLER, Sebastian; Syngenta Crop Pro Published: tection AG Schaffhauserstrasse, 4332 Stein (CH). ED¬ — with international search report (Art. 21(3)) MUNDS, Andrew; Syngenta Crop Protection AG Schaffhauserstrasse, 4332 Stein (CH). EMERY, Daniel; Syngenta Crop Protection AG Schaffhauserstrasse, 4332 Stein (CH). JUNG, Pierre, Joseph, Marcel; Syngenta Crop Protection AG Schaffhauserstrasse, 4332 Stein (CH). MUEHLEBACH, Michel; Syngenta Crop Protection AG Schaffhauserstrasse, 4332 Stein (CH). RAWAL, Girish; Syngenta Biosciences Private Ltd Santa Monica Works, Corlim, Ilhas, Goa 403 110 (IN). SEN, Indira; Syngenta Biosciences Private Ltd Santa Monica Works, Corlim, Il has, Goa 4031 10 (IN). SIKERVAR, Vikas; Syngenta Bio sciences Private Ltd Santa Monica Works, Corlim, Ilhas, Goa 403 110 (IN). (74) Agent: SYNGENTA INTERNATIONAL AG; Sch- warzwaldallee 215 B4.08. 152, 4058 Basel (CH). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (54) Title: PESTICIDALLY ACTIVE HETEROCYCLIC VATIVES WITH SULFUR CONTAINING SUBSTITUENTS (57) Abstract: Compounds of formula I (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a m an ner known per se. Pesticidally active heterocyclic derivatives with sulfur containing substituents The present invention relates to pesticidally active, in particular insecticidally active heterocyclic derivatives containing sulfur substituents, to intermediates for the preparation of those compounds, to compositions comprising those compounds, and to their use for controlling animal pests (including arthropods and in particular insects or representatives of the order Acarina). Heterocyclic compounds with pesticidal action are known and described , for example, in W O 201 2/086848, W O 201 3/01 8928, W O 201 5/0007 15 , and W O 201 5/1 2 1136. There have now been found novel pesticidally active heterocyclic 6/5-bicyclic ring derivatives with sulfur containing phenyl and pyridyl substituents. The present invention accordingly relates to compounds of formula I, wherein A is CH or N ; X is S , SO or S0 2; R is Ci-C4alkyl, Ci-C4haloalkyl or C 3-C6cycloalkylCi-C4alkyl; R2 is halogen, Ci-C6haloalkyl, Ci-C4haloalkylsulfanyl, Ci-C4haloalkylsulfinyl, Ci-C4haloalkylsulfonyl or Ci-C6haloalkoxy; X is O , S or NR3, wherein R3 is Ci-C 4alkyl; R 4 is Ci-C6alkyl, C 3-C6cycloalkylCi-C4alkyl, C 3-C6cyanocycloalkylCi-C4alkyl, C 3-C6halocycloalkyl, C3- Cealkynyl, C 3-C6haloalkenyl, C 3-C6halocycloalkylCi-C4alkyl, Ci-C4alkoxyCi-C4alkyl, Ci- C4alkoximinoCi-C4alkyl, Ci-C4alkylsulfanylCi-C4alkyl, Ci-C4alkylsulfinylCi-C4alkyl, Ci- C4alkylsulfonylCi-C4alkyl, Ci-C6cyanoalkyl, aminocarbonylCi-C4alkyl, Ci-C4alkylaminocarbonylCi- C4alkyl, di(Ci-C4alkyl)aminocarbonylCi-C4alkyl, di(Ci-C4alkyl)aminocarbonyl, hydroxycarbonyld- C4alkyl, Ci-C4alkoxycarbonylCi-C4alkyl, Ci-C6cyanohaloalkyl, aminocarbonylCi-C4haloalkyl, Ci- C4alkylaminocarbonylCi-C4haloalkyl, di(Ci-C4alkyl)aminocarbonylCi-C4haloalkyl, hydroxycarbonyld- C4haloalkyl, Ci-C4alkoxycarbonylCi-C4haloalkyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,3- difluoropropyl, trifluoromethyl, 2-fluoro-1 ,1-dimethyl-ethyl, 2-fluoroethyl, 1-fluorethyl, 2,2- difluoropropyl, 2-fluoro-1 -(fluoromethyl)ethyl, 2 ,2 ,2-trifluoro-1 ,1-dimethyl-ethyl, 1,1-difluoroethyl, di(Ci-C4alkyl)aminocarbonylCi-C4haloalkyl, Ci-C6cyano(Ci C4alkylsulfanyl)alkyl, Ci- C4alkoxycarbonylCi-C4(Ci C4alkylsulfonyl)alkyl, Ci-C4alkoxycarbonylCi-C4(Ci C4alkylsulfanyl)alkyl, aminocarbonylCi-C4 (Ci-C4alkylsulfanyl)alkyl, d i(Ci-C4alkyl)aminocarbonylCi-C4(Ci- C4alkylsulfanyl)alkyl, Ci-C4alkylaminocarbonylCi-C4(Ci C4alkylsulfanyl)alkyl, d i(Ci- C4alkyl)aminocarbonylCi-C4 (Ci-C4alkylsulfonyl)alkyl, tri-(C1-C6)alkylsilyl Ci-C4alkyl, C 1- C6alkylcarbonylCi C4alkyl, imino-C^C^Ikyl-oxo-C^C^Ikyl -S^iej-sulfane, Ci-C4haloalkylsulfonyl, propan -2-imine; o r R4 is is C 3-C6cycloalkyl which can be mono- o r polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, Ci-C4alkoxy and Ci-C4haloalkyl; o r R4 is phenyl o r a four- to six-membered heterocyclic ring system which can be partially saturated o r fully saturated , said ring system contains 1 to 2 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and said ring system can be mono- o r polysubstituted by substituents selected from the group consisting of halogen, cyano, Ci-C4alkyl, C 3-C6cycloalkyl, Ci-C4alkoxy, Ci- C4haloalkyl and oxo, and where the ring system is attached directly to the oxygen o r via a n Ci- C4alkylene chain; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I. Compounds of formula I which have at least one basic centre can form, for example, acid addition salts, for example with strong inorganic acids such as mineral acids, for example perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphorus acid o r a hydrohalic acid, with strong organic carboxylic acids, such as Ci-C4alkanecarboxylic acids which are unsubstituted o r substituted, for example by halogen, for example acetic acid , such as saturated o r unsaturated dicarboxylic acids, for example oxalic acid , malonic acid, succinic acid, maleic acid, fumaric acid o r phthalic acid, such as hydroxycarboxylic acids, for example ascorbic acid, lactic acid , malic acid, tartaric acid o r citric acid, o r such as benzoic acid, o r with organic sulfonic acids, such as Ci-C4alkane- o r arylsulfonic acids which are unsubstituted o r substituted, for example by halogen, for example methane- o r p-toluenesulfonic acid. Compounds of formula I which have at least one acidic group can form, for example, salts with bases, for example mineral salts such as alkali metal o r alkaline earth metal salts, for example sodium, potassium o r magnesium salts, o r salts with ammonia o r a n organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- o r tri-lower-alkylamine, for example ethyl-, diethyl-, triethyl- o r dimethylpropylamine, o r a mono-, di- o r trihydroxy-lower-alkylamine, for example mono-, di- o r triethanolamine. The alkyl groups occurring in the definitions of the substituents can be straight-chain o r branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, nonyl, decyl and their branched isomers. Alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, alkoxy, alkenyl and alkynyl radicals are derived from the alkyl radicals mentioned. The alkenyl and alkynyl groups can be mono- o r polyunsaturated. Halogen is generally fluorine, chlorine, bromine or iodine. This also applies, correspondingly, to halogen in combination with other meanings, such as haloalkyl or halophenyl. HaloalkyI groups preferably have a chain length of from 1 to 6 carbon atoms. Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2- trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2-difluoroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2- trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl. Haloalkenyl groups are alkenyl groups which are substituted by one or more of the same or different halogen atoms and are, for example, 2,2-difluoro-vinyl or 1,2-dichloro-2-fluoro-vinyl. Alkoxy groups preferably have a preferred chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, isobutoxy, sec-butoxy and tert-butoxy and also the isomeric pentyloxy and hexyloxy radicals. Alkylsulfanyl
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